Highland Vacations

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    Plan, book, and manage your trip all in one place

Find the Best Highland Vacation Packages

Highland Hotel Deals

Seasons Inn & Suites Highland
Seasons Inn & Suites Highland
2.5 out of 5
20 Central Blvd, Highland, IL
Fully refundableReserve now, pay when you stay
8/10 Very Good! (576 reviews)
"Bed a little to soft for my taste but both my traveling companions were fine with it."

Reviewed on Jun 15, 2025

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Seasons Inn & Suites Highland
Craftsman styled home in the heart of downtown Highland
Craftsman styled home in the heart of downtown Highland
Highland
9.8/10 Exceptional! (54 reviews)
Great Home, Great Location
"Six adults and one grandchild in town for a wedding. Loved having everybody under one roof! House was spotless on our arrival; Jennifer let us know we could check in early if we wanted to. House was well stocked and beds nice and comfy. Very convenient location, just a few minutes drive to church ..."

Reviewed on May 23, 2025

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Craftsman styled home in the heart of downtown Highland
The Loft on the Square
The Loft on the Square
Highland
Great place, highly recommend
"Family stay over holidays. Place was decorated and made us feel at home. Love the historical touches, would stay here again."

Reviewed on Dec 26, 2024

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The Loft on the Square
See all 97 properties in Highland
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does a Highland vacation package cost?
You can grab a vacation package to this popular destination on Expedia. But how much your vacation to Highland costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Highland?
You're likely to find lower prices and better availability in January, February and September. Browse our cheap Highland vacation packages and you could score some great off-season deals.
How many days is enough for Highland?
The ideal duration for your Highland vacation depends on what you'd like to see and do. Generally, a few days to a week will give you time to visit all the major sights and discover some hidden treasures along the way.
Is it worth booking a vacation package to Highland?
It's no wonder a Highland vacation is on the to-do list of many travelers. Leading attractions like Silver Lake Park are just the start of what you can explore here.
How to find the best Highland package deals?
Use Expedia's handy filters to find some tempting Highland package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or search for Highland package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Highland vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component individually. And you'll still enjoy the freedom to create a tailored Highland vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Highland?
If you have your Highland travel dates finalized, book as early as you can to snap up some awesome deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Highland?

  1. Choose the perfect time to travel: Your schedule, favorite season and the type of weather you like can all impact your decision on when to visit Highland.
  2. Set a budget: Consider expenses such as food, flights and transportation when working out how much to save for your trip to Highland. Then, select a property that works with your budget, whether that's an affordable stay or a deluxe getaway.
  3. Decide how long to go for: Now that you know more about Highland, you can figure out the right length of your break. Pull together a rough itinerary and allocate enough time to get through everything on your must-do list.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to pick a Highland vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.